Acetic Acid → HCID 12146683, compound

HRID 2416616Notes

Reaction equation

HRID 2416616 reaction equation
N[C:2]1[CH:3]=[C:4]([C:8]2[O:9][CH2:10][C:11](=[O:20])[N:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)[CH:5]=[CH:6][CH:7]=1.C=O.[C:23]([BH3-])#[N:24].[Na+].[C:27](O)(=O)C>C(#N)C.C(OCC)(=O)C>[CH3:27][N:24]([CH3:23])[C:2]1[CH:3]=[C:4]([C:8]2[O:9][CH2:10][C:11](=[O:20])[N:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:13]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 12146682HCID 12146682, compound

Product 1

HCID 12146683HCID 12146683, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(3-Aminophenyl)-4-phenyl-4H-1,3,4-oxadiazine-5(6H)-one (200 mg) obtained in Example 78 was dissolved in acetonitrile (5 ml), and 37% aqueous formaldehyde (1 ml) and sodium cyanoborohydride (250 mg) were added thereto, and acetic acid (0.15 ml) was added dropwise thereto over 5 minute, and mixed at room temperature for 6 hours. The reaction solution was diluted with ethyl acetate, washed with an aqueous saturated sodium bicarbonate and brine, and dried over anhydrous magnesium sulfate. After the drying agent was filtered off, the filtrate was evaporated and purified by silica gel chromatography (hexane/ethyl acetate system), to give the title compound (215 mg, 97%).

Workup

  1. additionmixed at room temperature for 6 hours
  2. washwashed with an aqueous saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter the drying agent was filtered off
  5. customthe filtrate was evaporated
  6. custompurified by silica gel chromatography (hexane/ethyl acetate system)

Sources & evidence

ORD record
ord-1493c7442dac43228bfba178ea17e097
Source dataset
uspto-grants-2004_11
Patent number
US06825192B1

Reaction notes

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